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This Is Why You Shouldn’t Join A Startup

By February 17, 2021No Comments

Feel like reading, instead of watching?

So today in Toronto, Canada, where I’m at right now… is a holiday.

It’s family day.

It is February 15th and anybody who’s anybody who’s in Canada right now is probably not working.

But I am.

And why am I working?

Well, because right now I work for a startup.

I want to talk about some of the myths, misconceptions, things that are over-exaggerated some of the things that probably aren’t discussed enough that you should pay attention to, if you choose to join a startup.

These are all things that you should consider if…

  1. You’re starting your career off in a startup.
  2. You’re pivoting in your career, and you want to go work for a startup.

If you like the idea of working in tech and disruptive industries and really like making a difference and you feel like you want to take your career in that direction, or if you’re looking to start your own thing and you’re looking to be an entrepreneur and run the company. you want to try something new.

Keep reading.

You see all the people in San Francisco, Silicon Valley, right?

The great jobs. The great pay. The kombucha. The ping pong tables. The bring your dogs to work.

All this fun stuff that you see in startup culture.

It’s glorified.

But first let me give you a little bit of context and a little bit of background about what’s going on in my life and why I have a little bit of authority to speak on this.

(And also — why I’m working on a holiday).

So right now, I do a lot of stuff, but in my actual nine to five I run sales and marketing for a startup within a much larger organization.

So, what does that mean?

If you go and look on my LinkedIn, you’ll see two companies.

You’ll see Grass Valley, which is a 60 plus year old company.

They do millions, hundreds of millions in revenue, a very large organization with thousands of employees.

And you’ll see another company ExciteM.

ExciteM is an OEM and an affiliate of Grass Valley.

We produce software solutions and SAAS solutions for them.

My job is to basically champion and bring to market these products through Grass Valley’s sales team as well as our own salesforce.

So, think about it as like a startup within a large company.

And it’s a lot of fun, a lot of work, but you still deal with the same things that a lot of people in startups deal with.

This means a lot of the time you have to figure stuff out on your own because when you’re building a startup, when you’re building any sort of new company from the ground up, you don’t have the resources or support.

And I also want to add this on right now, of course, we do have the ability to take items and take products through grass Valley and leverage their resources.

But at the end of the day, we’re still very much siloed and a lot of the stuff we do, we move very quickly.

We’re very agile and that means that we work on our own a lot.

And I’ve also ran my own consulting company with two other individuals.

So that was a startup as it got, building that from the ground up.

And part of what we did was that we consulted with startups.

So, a lot of emerging tech startups out of the University of Toronto.

We worked with them to build some of their marketing strategy there, take the market strategy, help founders really discover their brand and their voice and their founder story.

I was doing that for about two years, but I’ve worked with a lot of startups, worked with a lot of different types of entrepreneurs.

So, I wanted to speak on this topic because I’ve gone through the entire gamut of types of companies you can work for.

Basically, I’ve worked with the largest, I’ve worked for my own, and now I’ve worked for a startup within a large company.

So, I’ve seen the range of support and the range of types of work environments that you can be in… and startups are tough.

Starting your own thing is tough.

I want to highlight some of the biggest misconceptions of startups so that when you do choose to make them career pivot, or you choose to change, where you’re working, you can be educated.

Now first let’s speak about the benefits of startups, why you should join a startup, and then I’ll speak about some of the drawbacks or perhaps the misconceptions.

The Benefits of Joining a Startup.

When you join a startup, I would say the financial or the monetary benefit would be that you can get equity in that startup.

So, what does that mean?

When you join a large company, you’re just working for a salary or a paycheck.

Usually when you join a startup, they don’t have as much money as a large the company would, which makes sense. So, what they’ll do is they’ll give you the opportunity to have a piece of the company.

Now, it depends on how early you get in.

Startup could be a founder who just has an idea all the way through to a series B or C company, that has significant capital and is venture backed.

But there is a wide range of what is considered a startup and how much money they have.

And that being said, there still is usually a really strong opportunity for equity.

Especially if you come in at more senior positions or if you come in earlier on meaning they’re like a younger company, you can get a piece of that company.

So, what that means is when the company raises more money or perhaps the company sells or there’s some sort of exit event or there’s another round of funding or another series of funding when that happens.

If you have a piece of the company or you have equity or you have shares in the company, technically you should be able to get a payout.

Now I could go on about equity and shares and types of shares and preferential shares and what you should look for, if you’re actually looking to join a company, that’s giving you equity because a lot of the times there’s different types of shares and different types of equity.

And if you join the company and you don’t know what the company is giving you when they raise more money or when they sell to a larger organization, you may not actually get that much of a payout, but the Holy grail would be you join a startup, you get the equity and you get the right type of equity or right type of shares.

And then when they sell, you get, a lot of money and that’s something that people look for.

The Money

Now let’s talk about the misconceptions about startups.

A lot of companies don’t okay exit.

A lot of companies fail.

And if you’re looking to join a startup just for the payout, there’s a really good chance, it’s not going to happen.

And that’s the reality.

It’s very hard to get an exceptional payout from a startup.

You have to be lucky.

You have to be working for the right company.

You have to be joining them at the right time.

Stars have to align for this to happen.

The opportunity is very sexy, but don’t make that your only reason for joining startups.

Learning / Prestige

When you join a large company, you do your job and that’s pretty much it.

You stay in your lane and some people like that, some people don’t.

But if you want to learn a lot, if you’re younger in your career, if you want the type of education that is probably is even better than an MBA.

That’s why you’d want to join a startup.

Definitely better than any undergraduate degree.

If you work in a startup, you will learn an immense amount.

You will learn everything from sales to marketing, to finance, HR to fundraising, legal, negotiation.

You will learn absolutely everything because you’ll see it all.

Obviously, any good founder will still make sure that you have dedicated roles and responsibilities, so you can be successful as an employee of a startup.

But if you want to learn more and you want to discover more.

Nobody’s really ever going to stop you and you have direct access to literally all aspects of the business.

It depends on how big the startup is, but let’s assume you’re sub 50 individuals. You pretty much have the ability to communicate and network and learn from everybody who’s doing every function within a company.

This can be a ton of fun and it can really help you level up in your business acumen and your career and your general understanding of how businesses work, which can be beneficial if you ever want to advance in your career.

Because if you do want to advance your career, even at a larger company, it is smart to be able to have intelligent conversations about business topics that perhaps aren’t specifically in your field.

But with other executives in the organization or with other decision makers or stakeholders outside of your company also.

If you do ever choose to start your own thing, working for a startup is probably the smartest thing you’ll ever do because you will see all the functions of a business and in theory — how they all operate properly.

And that will give you a full 360 of what you’re going to have to know when you’re going and starting your owning.

I would say if we’re going to compare those two things, the payout and the opportunity to learn, the opportunity to learn is probably the most important and the most valid reason to join a startup.

There’s a very small chance you’re going to get a really significant pay, but the opportunity to learn will always be there.

That’s something that you really can use earlier on in your career.

If you have the energy, you have the time to invest.

Invest that time in a startup and learn, and that’s going to be the biggest benefit you’re going to take away.


The last item that people like to use as a reason as to why they want to go and work in a startup would perhaps be the clout.

They want to say they’re working for something innovative, something, forward-thinking — bleeding edge.

I would never make a career decision based on the sexiness of the industry.

I think that’s setting yourself up for disappointment and fail failure.

If you work for Google, if you work for Facebook yeah, it may be exciting to get the job, but just give it a month, give it three months.

And if you don’t like your manager, if you don’t like the work you’re doing, it’ll be just as shitty as if you’re working for a less sexy company where you also don’t like the people you work with, or you don’t like the work that you’re doing.

If you like the work that you’re doing and you enjoy the people you work with, and most importantly if you align yourself with a group of managers, peers that can elevate you and a lot.

And you want your work to align.

With your personal and professional goals, that’s where you’re going to be happy that’s where you’re really going to succeed.

That’s where you should be working.

Not just because the name of the company is the sexiest.

Because I know people that have gone into large companies and they leave because they got the job for the wrong reasons or they worked for the company for the wrong reasons.

So out of those three reasons… money, education/opportunity/learning and clout, the only valid reason that you would ever work for a startup would be the opportunity to learn.


I spoke a little bit about, starting your own thing.

I would say that those three reasons are very similar reasons as to why people start their own businesses.




Entrepreneurship is a whole other beast, but I would say that if you aren’t ready…

If you’re starting your own business for money, that’s the wrong reason.

You’ve probably won’t be very successful if you’re starting your own business for clout or for just to, perhaps elevate your own professional status or if you want to look cool with your friends or family.

That’s the wrong reason to start a business.

If you’re starting a business, knowing that you will be learning and that’s going to be the core of what you do, and you will only be successful if you learn to embrace and love learning and love the process.

And that’s why you want to start your own business.

That’s a good reason to start your own business and to become an entrepreneur.

Working in A Startup — The Reality

Now that we’ve covered some of the reasons why people join startups, let’s speak about the reality of working within a startup versus working in a large company.

And remember, I have worked in companies that were zero employees (when it was just me) to about three to five people, all the way through to around 50,000 people.

So, I’ve seen the gamut of places you can work at.

In a startup, it will be a grind.

You will have to put out the fires, you’ll have an extremely broad set of roles and responsibilities.

There’s a good chance that you won’t have the same budget or the same perks that you get in a large organization.

It’s tough.

Yes, there’s competing, opinions because in a startup it’s broad, you do everything.

Your roles and responsibilities are very diverse.

In a large organization you are coordinating across multiple different teams and multiple different stakeholders.

So, there’s a lot of specialization that you’re responsible for, as well as simultaneously roping in other specialists from around the organization.

However, on average, in a large organization, there’ll be less headaches, less, all-nighters less after 5:00 o’clock less before 9:00 am that you have to deal with.

In a startup, those are pretty normal.

Unfortunately, that’s the reality.

Again, this is not gospel.

This is not something that is an absolute rule across every single startup or large organization.

However, I have seen, and I’ve lived through both.

Startups definitely trend to more chaos, more work and a lot more stress for less reward, than the work-life balance, stability, and perhaps a little bit less stress and more support that you’d get at a large organization or a large company.

Culture Matters

Another common myth is that you’re joining perhaps a more forward-looking or fun, dynamic culture.

The reality is, is that you’re probably helping craft the culture.

So, your influence on the company is exponentially more important and valuable for the startup.

But also, you have to know, that what you bring in the energy you bring in and whatever you add on detract or change in the culture could become part of that company’s DNA.

Not everything is going to be figured out.

Not everything is going to be handed to you on a silver platter.

You are going to be contributing, crafting, and molding the culture as it grows.

Culture is incredibly important, especially at a startup level where you are molding and crafting the future of the organization.

So, if you don’t see value in culture, don’t join a startup because you’re not going to want to contribute, and it’s going to hurt the company and you’re going to feel friction.

If you’re joining a startup where the founder doesn’t see value in establishing a culture, you are going to feel lost and aimless.

And you’re going to feel like there’s a lack of vision and cohesiveness across the whole team and the whole company.

Career Growth

A third reason why a startup may not be what you expect is because it doesn’t offer clear career growth.

It doesn’t offer the same professional development.

It won’t offer a career path.

It’s incredibly more chaotic than working in a large company.

Benefits, schedule, vacations, personal/professional development.

You will find that some of these things lack in a startup environment, mostly because they haven’t had the resources or the time to properly invest in them yet.

So, know that in a startup environment, you will not have the same comfortable, cushy experience that you would have in a large company.

Things move quickly in startup land, and whether this works for you is entirely dependent on your personality type… if you can work in a chaotic environment.

But things will move quick.

Things will change.

Products, features, roles, responsibilities.

What your focus is one week may not be your focus in the next week.

Not saying this is great, and not saying that this is the hallmark of a successful startup, but it is the reality.

So, if you are going to work in a startup environment, be excited for change, embrace that it will happen most likely more often than not.

And that’s something that will make you a stronger professional.

If you can embrace change quickly.

(Remember what I said? This is for setting yourself up for your future).

Being in a startup is a learning experience to help set yourself up for your future career.

So, use the changes, use the chaotic environment to make yourself more resilient, to make yourself better in any situation.

Wherever your career takes you in five years.

You will have survived a chaotic environment.

You’ll have pivoted multiple times.

You will have dealt with all these different factors changing what you do on a daily, weekly basis.

And this’ll make you stronger in whatever you want to do.

If you’re going to start your own thing, or if you just want to be successful in a larger organization, or perhaps you’ll better understand what to look for when you join a startup and join a better startup in the future, these are all things that will help you just become a stronger professional.

Startups Fail

Last, but certainly not least.

Startups fail and they fail a lot.

Knowing that you have to be okay with saying “what happens if my company doesn’t exist in six months from now”.

Are you comfortable with that level of uncertainty?

Now I know that with COVID and whatnot, even people that had jobs that felt certain found out they weren’t so certain anymore.

Take this with a grain of salt, but startups in general, if you don’t know what to look for, when you’re joining a startup, you aren’t sure of the longevity or the funding or the run rate, or the other talent on the team, or the experience of the founder.

These are all things that you would have to actually look for when you’re joining.

But say you make a mistake, and you join the wrong company.

Know that it may not be around in six months.

So just keep all of these things top of mind.

Keep thinking about them as you look for other career opportunities and these things, to be honest, are all just magnified at when you decide to start your own business.

So, make your next career decision with confidence, but do it for the right reasons, and always know what you’re getting yourself into.


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